Amy's Introduction To Anal Play

As I recall this event in my life even now, I am getting damp between my legs. This is a true story of how I became so enthralled with anal play that now I won't end a night of sex, either by myself or with another, without some serious anal action.

Before I begin, please let me describe myself. My name is Amy. I am a single mom of two kids, a son and a daughter, both of whom are teens. I am 5'8", very tan, with long dark brown hair, and almond shaped dark brown eyes. I weigh around 135 lbs. Recently I began walking for exercise, I must say, I have become quite shapely in the ass and thighs. I am a 32b cup, which would be sad, except that at 41 years old, my little boobs are still so perfectly round and very soft and supple. They are accentuated by my wonderfully sensitive nipples, which get very rigid during sexual arousal and always give my level of excitement away, as I almost never wear a bra. I started shaving my pussy about 5 years ago and will never grow hair there again. I have had the most intense orgasms since I started shaving there and guys love it! (Girls too!! *giggle)

Up until about 5 years ago I'd thought that I had a pretty good sex life. However, anal sex for me was out of the question. Mom always said that that was a place not to be fooled with. I believed her and felt like I had plenty to offer with my pussy, my mouth, my hands, and my great tits!

One unfortunate day led me to a level of sexual pleasure greater than any I'd ever dreamed of. While on my way to work one day I suddenly felt ill. I had a tremendous pain in my lower back on my right side. It hurt so badly that I began to cry and did not know what was wrong. I drove home and called my neighbor Sally. She ran over to my house and immediately began rifling through my purse to find my address book and call my doctor. She called him and explained how much pain I was in. He said I should come to see him right away. Sally drove and tried to comfort me as I sat in the passenger seat writhing in pain and worrying that something horrible was wrong with me.

When we arrived I was still in great pain and could not help crying. The nurse rushed me into a room with Sally at my side. My doctor came into the room and in no time he began to poke and prod and roll me onto my side. He asked me if I was having my period and I told him no, and that I had just finished with my period last week. He seemed to know then rather quickly what was ailing me and asked me if I had ever had a kidney stone. I looked at him funny and said "No."

He said that he fully believed that was all that was wrong with me and that I would be in a lot less pain as soon as the kidney stone moved out of that place that was hurting me and began to move toward my bladder. He did suggest that there might be some more pain as I passed the stone, but it should be ok. To be absolutely sure however he sent me home (with some good pain pills by the way) and asked me to return the following day to have some X-rays done. He continued, "But", and he seemed to say "But" with a tight-lipped grin. "The reason you will need to return tomorrow is that you will need to fast over night. No food or drink after 8:00 tonight, and give yourself an enema before you come in. That way you will clean your bowels of any obstructions allowing me to see if there is anything else causing you this pain."

Inside I gasped. Did he say enema? A million things went through my mind. An enema seemed medieval! Do they still do that I asked myself? He looked at me noticing my concern and recommended a drug store that he knew could provide me with the enema supplies that I would need. He also said reassuringly, that everything was going to be ok and he was pretty sure that a kidney stone was my only problem.

I left his office still feeling awfully bad. On the drive home Sally offered to run into the drug store and purchase the enema stuff I would need. I felt really embarrassed, but hey, us women go through a lot, and I thought, well ok, this is just another crappy thing to happen. (No pun intended.)

While Sally was in the store, my mind raced with what I was going to have to do. How on earth am I going to give myself an enema? I can't even see back there and this was surely going to hurt. I kept trying to picture myself struggling to get this thing up my ass, and doing it right, and not hurting myself, and wondering if it was going to work, when Sally bounced back into the car and cheerfully announced that she had what I needed.

As we drove the rest of the way home I decided that I was going to need help. Sally is such a great friend that I thought I should ask her to help me. I was afraid that she would think I was weird, but I really had no other choice. My pride aside I suddenly blurted out, "Sally would you help me do this?" Before she could say anything, I repeated, "Would you help me do this enema thingy?"

Sally looked at me and for a moment, I really thought she was going to scream, "NO WAY!!" But Sally, being the true friend that she is, just looked me in the eye and asked, "Are you sure Amy? Are you sure you want me to help you? I have never done this before ever." she exclaimed.

I said "Well neither have I;" and then began to plead, "please Sally help me do this." I could feel the tears welling up inside and she finally agreed.

"Oh thank you so much…" I said as I reached out and squeezed her hand.

Back at my house she helped me out of my clothes. When I was down to just my panties, Sally reached into my drawer and tossed me a nighttime, extra long sleep shirt. I quickly threw it over my shoulders, pulled my hair out from within, and hopped into bed. Sally brought me some water to take the pills that the doctor gave me, and soon I was fast asleep.

I woke up later that evening. Sally had come over and fed the kids and told them what happened to me. I remember feeling that the worst of my pain was gone now and I thought that maybe the whole thing was over. I rolled over slowly and really didn't feel anything. I thought maybe the worst of it was over. I slowly walked out of the bedroom and found the kids watching TV. They ran to me, hugged me, and asked if I was ok. They told me that Sally had fed them and left me a note. I grabbed the note from the kitchen counter and read it.

"Amy, I hope you are feeling better. I made the kids dinner and I will come by tomorrow morning to help you before your X-rays."

I remember smiling and thinking that she didn't actually say "Help me with the enema." I was feeling groggy enough to go back to sleep, so I took another pain pill just in case and trotted off back to bed.

The next morning I woke up in time to see the kids off to school. About two minutes later Sally showed up and asked if I had coffee going already. I said "No, I can't eat or drink anything before my X-ray remember?"

She apologized and asked if I minded if she had some. I said that I didn't mind and she promptly began to make coffee. She asked how I was feeling and I could tell that she was as nervous as I was. I told her that I was a little scared and thanked her again for helping me. She smiled and said, "That's what friends are for."

While waiting for the coffee to be ready, Sally reached into the bag from the drugstore and pulled out a box. She opened the box and out came an honest to goodness, real life enema bag. I immediately thought that I had seen that very thing before and couldn't remember where. Anyways, the top looked like a cap that was also an oversized hook, and I deduced this was where you open it to put the fluid in. At the bottom was a long clear hose that coiled up. I remember thinking for just a second, "HOLY SHIT you're not putting that hose thingy inside me!" Then at the other end I noticed a long tapered nozzle. It looked to be about 4 or 5 inches long and pretty narrow. It had several holes in the end and it all became painfully clear. This was the part that was going to have to be inserted into my ass! Back at the bag end of the hose there was a clamp thingy attached to the hose and later we learned that this was to control the flow.

Sally plopped down onto the barstool in the kitchen and started reading out loud. We giggled like schoolgirls reading the directions. There were even some crude drawings of how best my body should be situated to have this assault performed. When she was done reading the directions, I felt like I had been holding my breath the whole time. Sally reached into the bag again and pulled out a small tube of what I immediately recognized as water based KY jelly.

The directions from the enema box recommended a very mild solution of warm soapy water. They also recommended that the water be as warm as I thought I could stand it. Sally, armed with the stuff, motioned for us to move to the bathroom. I started to feel really scared and telling Sally this, she put the things down and smiled. She then hugged me and said, "We'll get through this together ok?" I have to admit I felt a little better and lead her to my master bathroom.

I had always thought that Sally was a very beautiful woman. She was 6 years younger than me and at 35 had a great body. She was about 5'6", and I guessed she weighed about 120 lbs. Her ass made just about anything she wore look great! She had light brown hair that went down to just past her shoulders. Her boobs were exactly like mine, tiny, but full and supple. We had seen each other topless several times before, and I always thought I would love to see her nipples hard. Her eyes were a lighter shade of brown than mine, but very alluring, and she knew how to accentuate her features with make-up just right. I loved her smell, yet never remembered to ask her what perfume she wore.

I was still wearing the long t-shirt and panties as we entered the bathroom when suddenly I realized that I was going to have to strip. As I removed my panties, Sally gasped and then kinda mumbled saying, "I didn't know you shaved down there."

I winked at her, smiled, and jokingly said, "You never asked."

We both laughed and then I realized that I should probably remove my long t-shirt as well. I tossed my clothes over toward the hamper and felt content that they'd made it close enough. Standing totally naked in front of Sally I felt slightly uncomfortable and I thought to myself that she should have to be naked too! Then I realized that even though we had just read the directions, I really wasn't sure what to do next.

Before I knew it, Sally seemed to take charge. She turned on the tub and made the water very warm. She suggested that I feel it to make sure I was ok with the temperature. I reached my hand into the flowing water and at first it felt kinda hot, but then I thought it should be ok. Sally opened the top of the enema bag and placed it under the water. When it was half way full she pulled it out and put in a squirt of liquid Dove bath soap. She placed the enema bag under the flow again and filled it up. Then she placed the cap onto the bag and began to shake it getting the mixture into a good soapy solution.

I felt a little cold standing there naked and realized that my nipples had hardened. I also felt a little aroused standing there totally naked in front of Sally. I wondered if she felt as uncomfortable as me, but realized hey, she's not the one standing here naked!

Suddenly Sally spoke and brought me back to reality. She said, "Ok get into the tub and get on your hands and knees."

I hadn't really thought about doing it inside the tub, but it seemed to make the most sense. I felt like a little girl being told what to do, but I climbed in anyhow. Sally hung the enema bag up on the shower curtain rod and let the hose kinda hang down. She placed the nozzle on a towel on the floor. Sally reached for the KY jelly and sighed with a resigned "Ok."

Sally seemed to be unsure of what to do next. I asked her "What's up?"

I realized that she was trying to find the words to say what she needed to do. I thought to myself, why don't you just say you need to squirt some KY jelly on your finger and shove it in my ass! Then realizing her discomfort too I said, "I know, its ok."

She got up and for a second I thought she was going to run out of the room. She grabbed another towel from the vanity however and tossed it to me in the tub. "Put this down and lay your head on it. This will be more comfortable for you and make it easier for me to lubricate you."

I remembered that that was what the directions had said and smiled, thinking I'm glad she paid attention. I spread my knees to either side of the tub and as I laid my head down I felt totally exposed. My ass cheeks had spread and my pussy was right there. I tried to look at Sally but really couldn't see much. I started to realize that I was getting a little wet. I could actually feel my pussy getting a little squishy inside and I hoped that my wetness was not showing. I thought to myself gawd I wish I could just masturbate right here!

It seemed like forever before Sally did anything, and I was just thinking about raising my head to see what she was doing, when suddenly I felt her hands on my ass. They were the softest hands I had ever felt on my bottom. I jumped and Sally giggled and said, "Oh I'm sorry, I didn't mean to make you jump."

"It's ok" I mumbled, and tried to relax.

Her hands went right to work. She placed the palm of her left hand at the very bottom of my back just above my ass. Her thumb and fingers then began to spread my ass cheeks apart. Her other hand kind of pushed my ass cheeks further apart as she seemed to be looking for the exact spot to place the lubrication. I could feel myself getting kinda tense. It's funny I didn't feel this exposed and vulnerable giving birth to my two children!

I guess she was just in for a reconnaissance mission because suddenly she let go and neither of her hands were touching me. She said, "Ok honey I'm going to put some of this jelly on you now ok?"

I wanted to scream ALRIGHT ALREADY, but instead I sort of managed a humble "Ok."

Before I knew it, her left hand took over its position again right above my ass. This time however, her hand seemed to be a little more forceful. Her thumb and fingers really spread my ass cheeks wide. I felt like my little ass was opening right there for her. I could also feel my pussy lips part slightly and just knew that Sally could tell that I was very wet! As she spread me so deftly I could feel a little cool air touch me when suddenly it happened. Sally's lubricated finger found my anus like she was placing her finger on a button. I immediately and instinctively gasped out loud and lurched forward. Her warm, soft, greased finger seemed to launch me into orbit. I jumped so far forward in fact, her hand lost its grip on my ass cheeks. She burst out laughing, and then so did I. She said, "I told you it was coming!"

I apologized and kinda backed up to where I was by scooching back with my ass in the air and my head down. Sally said with a giggle in her voice, "Shall we try this again?"

As she said this, she rather forcefully but playfully slapped my butt and I could feel a little sting, as my cheek seemed to reverberate under her minor assault. Now I was getting excited. Although I had never let another man or woman go near my sacred ass hole I wasn't entirely against some playful spanking. In fact it was just the week before when another friend of mine decided that I needed a spanking after I had locked his keys in his car for the second time in a month. (That's another story that I may retell some time down the road.)

So there I was on my knees, head down, knees spread to the edges of the tub, and my ass high up in the air. My ass was so totally exposed, and feeling my pussy near to gushing with squishiness, I felt so very naughty. Here I was having my neighbor and good friend seeing me like this and all I could think about was how excited I was! Sally began again. "Ok honey here we go." She added some more jelly to her finger and reached for me again. I could feel her left hand at the now familiar place at the top of my ass and using her thumb and fingers as before, she spread my ass wide open. Her other hand had several fingers gooped up with the jelly and she began to ever so slowly touch my ass. Her fingers were softer than silk and felt so warm and wonderful that I felt myself sigh with relief that she was finally getting started.

She slowly rubbed the jelly around my tiny ass hole. Her fingers worked in small gentle circles around my tiny brown hole and the excitement level for me was almost too much! I was so embarrassed. I could feel my body letting go and actually craving her touch. By now my pussy was dripping and I was sure it had to be totally obvious to Sally. Yet she stayed true to the task and could sense my coming at ease with her touching me in my formally forbidden place. Sally added some more jelly to my wanton ass. She was working it to relax so it could be ready for the assault. I knew it would come soon and sure enough I could feel Sally's finger start to slowly push into my ass hole. Her left hand worked hard to keep my ass cheeks spread and I suddenly realized that since she started, Sally had said nothing. She was being very quiet. I wondered to myself what she must be thinking. I knew my pussy was aching to be touched and I wondered if Sally was getting these same feelings seeing me like this. Playing with my ass hole had to be turning her on at least a little! Her finger seemed to glide right inside my tiny brown hole. It felt AWESOME!

Before I knew it she had pulled it out. Sally added some more jelly and returned to my ass. This time she didn't linger outside my ass too long and began to push her finger inside me again. It was such a tiny invader and it felt so good I could feel her finger pushing deeper and deeper inside my ass. Sally began pumping her finger in and out of my ass slowly, working the jelly all around inside as she did. She surprised me by finally speaking as she did this. "How does this feel?" she asked. As her finger pushed in and out of my ass seemingly with ease I stuttered as I tried to say something. I tried again and this time managed to say that if felt really really good. All at once I realized that I said that with the most eagerly sexual tone, and began to wiggle my ass toward her invading finger. My arms were tucked under me as I unwittingly began to rub one of my nipples. It just felt natural and I guess my inner sexuality took over.

Sally surprised me again by calling attention to the fact that my pussy was glistening with my juices and she said, "Amy?! Is this getting you excited?!"

I know there was a long pause as I thought about what to say. "I can't help it Sally," I exclaimed, having to clear my throat as I said it.

Sally said, "Well you ought to be here where I am! This is soo HOT!"

Raising my head slightly I looked over at Sally. She had a wickedly wild look in her eyes and I decided right then and there that I needed some release. I swallowed hard and nervously questioned, "Sally? You're not going to believe this but this feels sooo good! Please let me make myself cum?!"

I immediately panicked and thought maybe I shouldn't have said that but felt a huge sigh of relief as I noticed a smile come over her face. She then really surprised me and asked, "Do you want me to leave you alone for a minute?"

Louder than I wanted to I said, "NO! Please stay? Please keep doing that to my ass!"

Before she could even answer my right hand dove toward my sopping pussy. I didn't even realize it before, but my pussy lips had become quite swollen. It felt sooo good to reach two fingers deep into my pussy. I worked them in and out a few times pushing deeper and deeper each time. I felt like I was fucking myself and it felt fantastic! I could hear my fingers squishing inside my pussy as I worked them faster and harder. Most times I actually felt Sally's finger inside my ass at the same time with my fingers inside my aching pussy! This felt so incredible; I know she could feel it too!! I thought to myself what have I been missing? I imagined what it would feel like to have two cocks working me at the same time! Mmmmm yes, two huge thick cocks inside me at once. Cocks that were much larger and longer and thicker than Sally's and my fingers!! I decided that this was a new goal for me!